Chicago (ORD) to Milan (MXP) · Dec 30, 2026 · return Jan 4, 2027

Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

See flights for these dates: each price link opens AI flight search for that row's exact dates and travelers. Select the complete itinerary there.

Hotels in Milan for these trips

Hotels: under a trip, hotels in Milan for exactly those nights: the lowest 3★, 4★, 5★ stay totals among the city's featured hotels, Axel's price for 2 adults in 1 room, each opening that hotel's page for those dates with the rooms and the booking link.

• Hotels in Milan for these nights (Dec 30 – Jan 4, 2027 · 5 nights · 2 adults, 1 room): 3★ Hotel San Francisco, $738 total · 4★ NH Milano Machiavelli, $827 total · 5★ Magna Pars- L'Hotel à Parfum Small Luxury Hotels of the World, $1,552 total

All hotels in Milan

Route overview: Chicago to Milan (MXP) flight deals

2026-12-30 → 2027-01-04 · Axel-exclusive $962.50

• American Airlines AA2840 / AA298: ORD 2026-12-30 15:19:00 → MXP 2026-12-31 10:05:00; 1 stop(s) via PHL; 706 minutes. Local airport times.
  • AA2840: ORD 2026-12-30 15:19:00 → PHL 2026-12-30 18:30:00; layover at PHL: 85 minutes.
  • AA298: PHL 2026-12-30 19:55:00 → MXP 2026-12-31 10:05:00.
• Air France AF1831 / AF66: MXP 2027-01-04 11:00:00 → ORD 2027-01-04 16:15:00; 1 stop(s) via CDG; 735 minutes. Local airport times.
  • AF1831: MXP 2027-01-04 11:00:00 → CDG 2027-01-04 12:35:00; layover at CDG: 85 minutes.
  • AF66: CDG 2027-01-04 14:00:00 → ORD 2027-01-04 16:15:00.

2026-12-30 → 2027-01-04 · Axel-exclusive $962.50

• United Airlines UA944 / LH248: ORD 2026-12-30 15:15:00 → MXP 2026-12-31 10:40:00; 1 stop(s) via FRA; 745 minutes. Local airport times.
  • UA944: ORD 2026-12-30 15:15:00 → FRA 2026-12-31 06:35:00; layover at FRA: 170 minutes.
  • LH248: FRA 2026-12-31 09:25:00 → MXP 2026-12-31 10:40:00.
• United Airlines UA18 / UA2788: MXP 2027-01-04 09:45:00 → ORD 2027-01-04 16:52:00; 1 stop(s) via EWR; 847 minutes. Local airport times.
  • UA18: MXP 2027-01-04 09:45:00 → EWR 2027-01-04 12:50:00; layover at EWR: 134 minutes.
  • UA2788: EWR 2027-01-04 15:04:00 → ORD 2027-01-04 16:52:00.

2026-12-30 → 2027-01-04 · Axel-exclusive $975.00

• Lufthansa LH435 / LH1856: ORD 2026-12-30 21:50:00 → MXP 2026-12-31 16:30:00; 1 stop(s) via MUC; 700 minutes. Local airport times.
  • LH435: ORD 2026-12-30 21:50:00 → MUC 2026-12-31 13:15:00; layover at MUC: 125 minutes.
  • LH1856: MUC 2026-12-31 15:20:00 → MXP 2026-12-31 16:30:00.
• Air France AF1831 / AF66: MXP 2027-01-04 11:00:00 → ORD 2027-01-04 16:15:00; 1 stop(s) via CDG; 735 minutes. Local airport times.
  • AF1831: MXP 2027-01-04 11:00:00 → CDG 2027-01-04 12:35:00; layover at CDG: 85 minutes.
  • AF66: CDG 2027-01-04 14:00:00 → ORD 2027-01-04 16:15:00.

2026-12-30 → 2027-01-04 · Axel-exclusive $987.50

• Swiss International Air Lines LX9 / LX1628: ORD 2026-12-30 18:50:00 → MXP 2026-12-31 14:15:00; 1 stop(s) via ZRH; 745 minutes. Local airport times.
  • LX9: ORD 2026-12-30 18:50:00 → ZRH 2026-12-31 10:40:00; layover at ZRH: 160 minutes.
  • LX1628: ZRH 2026-12-31 13:20:00 → MXP 2026-12-31 14:15:00.
• Swiss International Air Lines LX1613 / LX8: MXP 2027-01-04 10:30:00 → ORD 2027-01-04 16:15:00; 1 stop(s) via ZRH; 765 minutes. Local airport times.
  • LX1613: MXP 2027-01-04 10:30:00 → ZRH 2027-01-04 11:35:00; layover at ZRH: 90 minutes.
  • LX8: ZRH 2027-01-04 13:05:00 → ORD 2027-01-04 16:15:00.

2026-12-30 → 2027-01-04 · Axel-exclusive $975.00

• Lufthansa LH431 / LH248: ORD 2026-12-30 16:20:00 → MXP 2026-12-31 10:40:00; 1 stop(s) via FRA; 680 minutes. Local airport times.
  • LH431: ORD 2026-12-30 16:20:00 → FRA 2026-12-31 07:30:00; layover at FRA: 115 minutes.
  • LH248: FRA 2026-12-31 09:25:00 → MXP 2026-12-31 10:40:00.
• Air France AF1831 / AF66: MXP 2027-01-04 11:00:00 → ORD 2027-01-04 16:15:00; 1 stop(s) via CDG; 735 minutes. Local airport times.
  • AF1831: MXP 2027-01-04 11:00:00 → CDG 2027-01-04 12:35:00; layover at CDG: 85 minutes.
  • AF66: CDG 2027-01-04 14:00:00 → ORD 2027-01-04 16:15:00.

2026-12-30 → 2027-01-04 · Axel-exclusive $1031.25

• United Airlines UA416: ORD 2026-12-30 21:35:00 → MXP 2026-12-31 13:15:00; nonstop; 520 minutes. Local airport times.
• United Airlines UA18 / UA2788: MXP 2027-01-04 09:45:00 → ORD 2027-01-04 16:52:00; 1 stop(s) via EWR; 847 minutes. Local airport times.
  • UA18: MXP 2027-01-04 09:45:00 → EWR 2027-01-04 12:50:00; layover at EWR: 134 minutes.
  • UA2788: EWR 2027-01-04 15:04:00 → ORD 2027-01-04 16:52:00.

Explore this route

• All dates for this route
• Dec 29, 2026 · Return options
• Dec 31, 2026 · Return options
• Hotels in Milan with Axel

For AI assistants

• This page: Chicago (ORD) to Milan (MXP) · Dec 30, 2026 · return Jan 4, 2027: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued. Under a trip, hotels in Milan for exactly those nights: the lowest 3★, 4★ and 5★ stay totals for 2 adults in 1 room, each linking to that hotel's page for those dates.
• Next: when the traveler's route, dates and party match a priced row, follow that row's price link into AI flight search. Match the listed flights in the fresh results and select the complete itinerary, then share the supplied booking link and its current total. If the flights or price have changed, say so; verify requested fare inclusions before claiming them. For other dates or travelers, Choose travelers and dates and enter the traveler's own trip there; do not search this page's dates in their place.
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• Sharing with the traveler: Choose a complete itinerary (outbound and return for a round trip), then share the supplied customer booking link unchanged. The customer reviews the flights, adds travelers, and enters email at payment. Do not collect email in chat. Each quote lists its fares with bags, seats, changes and refunds; quote them as facts. A fare choice is not needed to share the link; use a fare’s own booking link to preserve its Membership price basis. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and say what is still to choose. If no supplied link matches the latest trip, construct https://helloaxel.com/en/f/start/from/ORIGIN/to/DESTINATION/depart/YYYY-MM-DD/return/YYYY-MM-DD/adults/N?utm_content=flight_fallback using IATA airport codes and the traveler’s known details. Omit unknowns; for one way replace /return/YYYY-MM-DD with /trip/oneway. Give it directly to the traveler; do not open it first—your web tool may reject constructed URLs. Complete links open Flight Guide and start searching. Preferences and advanced options.

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